Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:10 UTC |
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Update date | 2020-09-17 15:42:08 UTC |
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Primary ID | FDB001931 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Succinic acid |
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Description | Succinic acid is a four-carbon acyclic dicarboxylic acid. It is a white, odorless solid with a highly acidic taste. It is used as a flavoring agent, contributing a sour and astringent component characteristic of the umami taste (PMID:21932253). The anion, succinate, is a key component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate dehydrogenase (SDH) plays an important role in mitochondrial function, being both part of the respiratory chain and the Krebs cycle. SDH, with a covalently attached FAD prosthetic group, is able to bind several different enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the entire Krebs cycle. Succinic acid has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid is also a microbial metabolite. Indeed, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter sp., Acinetobacter sp., Proteus mirabilis, Citrobactes frundii, Enterococcus faecalis (PMID: 22292465). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465; PMID: 18191255; PMID: 26360870). Succinic acid, or its anion succinate, is used as an excipient in pharmaceutical products to control acidity or as a counter ion. Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. In 2004, succinic acid was identified by the Department of Energy of the United States of America as one of twelve molecules that can be produced from plant sugars through biological or chemical processes and that have a potential to subsequently be converted to a number of high-value bio-based chemicals or materials. |
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CAS Number | 110-15-6 |
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Structure | |
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Synonyms | Synonym | Source |
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1,2-Ethanedicarboxylic acid | ChEBI | Acide butanedioique | ChEBI | Acide succinique | ChEBI | Acidum succinicum | ChEBI | Amber acid | ChEBI | Asuccin | ChEBI | Bernsteinsaeure | ChEBI | Butandisaeure | ChEBI | Butanedionic acid | ChEBI | Dihydrofumaric acid | ChEBI | e363 | ChEBI | Ethylenesuccinic acid | ChEBI | HOOC-CH2-CH2-COOH | ChEBI | Spirit OF amber | ChEBI | 1,2-Ethanedicarboxylate | Generator | Butanedionate | Generator | Dihydrofumarate | Generator | Ethylenesuccinate | Generator | Succinate | Generator | 2-Acetamido-2-deoxy-D-glucose | HMDB | D-GlcNAc | HMDB | N-Acetyl-D-glucosamine | HMDB | N-Acetylchitosamine | HMDB | N Acetyl D glucosamine | HMDB | 2 Acetamido 2 deoxy D glucose | HMDB | 2 Acetamido 2 deoxyglucose | HMDB | 2-Acetamido-2-deoxyglucose | HMDB | Acetylglucosamine | HMDB | 1,4-Butanedioate | HMDB | 1,4-Butanedioic acid | HMDB | Katasuccin | HMDB | Wormwood acid | HMDB | 1,2 Ethanedicarboxylic acid | HMDB | 1,4 Butanedioic acid | HMDB | Potassium succinate | HMDB | Succinate, ammonium | HMDB | Butanedioic acid | HMDB | Succinate, potassium | HMDB | Ammonium succinate | HMDB | 1,4-BUTANEDIOIC ACID (SUCCINIC ACID) | biospider | 1cze | biospider | Acid of amber | biospider | Amber acid, butanedioic acid, ethylenesuccinic acid | biospider | Butanedioic acid (9CI) | biospider | Butanedioic acid diammonium salt | biospider | Butanedioic acid, 9CI | db_source | E363 | db_source | Ethane-1,2-dicarboxylic acid | db_source | Ethanedicarboxylic acid | biospider | Ethylene dicarboxylic acid | biospider | Ethylene succinic acid | biospider | FMR | biospider | MAE | biospider | Sal succini | biospider | Salt of amber | biospider | SIN | biospider | Spirit of amber | biospider | SUC | biospider | SUCC | biospider | succinate, 9 | biospider | Succinellite | biospider | Succinic acid (8CI) | biospider | Succinic acid, acs | biospider | Succinicum acidum | biospider | Succinicun acidum | biospider | Wormwood | biospider |
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Predicted Properties | |
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Chemical Formula | C4H6O4 |
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IUPAC name | butanedioic acid |
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InChI Identifier | InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8) |
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InChI Key | KDYFGRWQOYBRFD-UHFFFAOYSA-N |
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Isomeric SMILES | OC(=O)CCC(O)=O |
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Average Molecular Weight | 118.088 |
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Monoisotopic Molecular Weight | 118.02660868 |
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Classification |
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Description | Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Dicarboxylic acids and derivatives |
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Direct Parent | Dicarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 40.68%; H 5.12%; O 54.19% | DFC |
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Melting Point | Mp 184-185° | DFC |
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Boiling Point | Bp 235° dec. | DFC |
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Experimental Water Solubility | 83.2 mg/mL at 25 oC | YALKOWSKY,SH & HE,Y (2003) |
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Experimental logP | -0.59 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa2 5.7 (25°, H2O) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-05di-9100000000-c629bea41d0d3d896425 | Spectrum | GC-MS | Succinic acid, 2 TMS, GC-MS Spectrum | splash10-0002-0920000000-f286e6204a4163b823ba | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-bf336910bb37d7f78140 | Spectrum | GC-MS | Succinic acid, 2 TMS, GC-MS Spectrum | splash10-006t-9800000000-df5ff4e8457d2d4ef919 | Spectrum | GC-MS | Succinic acid, 2 TMS, GC-MS Spectrum | splash10-00c1-3930000000-3cc18e719822b5af661a | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-004i-9000000000-93b4807ae6275a3e59d7 | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-0kos-9100000000-f1df0903a24c305e68ec | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0910000000-300c33b39fb991b5a73e | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0920000000-f286e6204a4163b823ba | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-bf336910bb37d7f78140 | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-006t-9800000000-df5ff4e8457d2d4ef919 | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-00c1-3930000000-3cc18e719822b5af661a | Spectrum | GC-MS | Succinic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-f838d863ee7c2b111f02 | Spectrum | Predicted GC-MS | Succinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00xr-9300000000-f0644daf4fbb11fcc2dc | Spectrum | Predicted GC-MS | Succinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00dj-9710000000-ff8325384b9eefd19106 | Spectrum | Predicted GC-MS | Succinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Succinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Succinic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Succinic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Succinic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-00di-9300000000-f9dc864d93a09d3074f9 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00di-9300000000-76c151de384928b2256f | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-01b9-7900000000-51d2341c097f04827944 | Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-004i-9000000000-93b4807ae6275a3e59d7 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-03dj-0971010000-37d214dc7a8fdc26116b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-014i-9000000000-249222ac742c1634cec9 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-00di-9000000000-6897d49472dba6a34a27 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0udi-0490000000-d138f8023125921b4b82 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-1900000000-4ffdabe5bde527b66982 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00di-9100000000-c20baa818f5ff5f678c1 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-00di-9000000000-7a49a18aa6fcb2540a12 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-00di-9000000000-9955aeb0e5a9f88ae70e | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-00di-9000000000-7e1f195f111b4eafb4fa | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-00xr-9400000000-e50afc90e20cd420ba9b | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-00xr-9600000000-43167f2549cbb5d5f7e8 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-1900000000-4ffdabe5bde527b66982 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9100000000-7a8bfa543dc087bea06d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-fdec6c7458176f3cbeb8 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-9955aeb0e5a9f88ae70e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0gb9-2900000000-9d959a53833b07094158 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0l6r-9600000000-c367e11e737714d41418 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-056r-9000000000-e65aa602a8293debec36 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-2900000000-e1f840494c9003279869 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-7900000000-1089efd4a3469bcf14f1 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0604-9000000000-0e0e60bb202ffb004894 | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 1078 |
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ChEMBL ID | CHEMBL576 |
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KEGG Compound ID | C00042 |
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Pubchem Compound ID | 1110 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15741 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00139 |
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HMDB ID | HMDB00254 |
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CRC / DFC (Dictionary of Food Compounds) ID | CBG32-P:CBG32-P |
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EAFUS ID | 3557 |
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Dr. Duke ID | SUCCINIC-ACID |
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BIGG ID | 33633 |
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KNApSAcK ID | C00001205 |
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HET ID | SIN |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1040431 |
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SuperScent ID | 1110 |
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Wikipedia ID | Succinic acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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additive | 64047 | Any substance which is added to food to preserve or enhance its flavour and/or appearance. | DUKE | anti feedant | | | DUKE | bruchiphobe | | | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | dye | 37958 | | DUKE | perfumery | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | CHEBI |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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sour |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| odorless |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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